Category: 1422772-78-8

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1422772-78-8

Step 5. Methyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate. To a 0 C. suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (145 g, 602 mmol) in MeOH (1.5 L) was added dropwise SOCl2 (93 g, 781 mmol) over a period of 40 min. after the addition, the resulting mixture was heated to reflux for 4 hours, which time suspended solution became clear and then yellow solid was precipitated. TLC (petroleum ether/EtOAc, 1:1) showed starting material was consumed completely. The reaction mixture was evaporated to dryness, which was triturated with MTBE to give methyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate (109 g, 71%) as a yellow solid.

According to the analysis of related databases, 1422772-78-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thorarensen, Atli; Brown, Matthew Frank; Casimiro-Garcia, Agustin; Che, Ye; Coe, Jotham Wadsworth; Flanagan, Mark Edward; Gilbert, Adam Matthew; Hayward, Matthew Merrill; Langille, Jonathan David; Montgomery, Justin Ian; Telliez, Jean-Baptiste; Unwalla, Rayomand Jal; US2015/158864; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C7H4BrN3O2

To a suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (Example 83 Step 1, 145 g, 602 mmol) in MeOH (1.5 L) at 0C was added thionyl chloride (93 g, 781 mmol) dropwise over 40 minutes. The reaction was heated to reflux for 4 hours before cooling and concentrating in vacuo. The resulting solid was triturated with TBME to afford the title compound as a yellow solid (109 g, 71%) that was taken directly on to the next step.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; THORARENSEN, Atli; BROWN, Matthew Frank; CASIMIRO-GARCIA, Agustin; CHE, Ye; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; HAYWARD, Matthew Merrill; TELLIEZ, Jean-Baptiste; UNWALLA, Rayomand Jal; TRUJILLO, John I.; LIANG, Sidney Xi; (212 pag.)WO2016/178110; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1422772-78-8 as follows. HPLC of Formula: C7H4BrN3O2

Ice bath,(COCl) 2 (7.5 mL) and DMF (0.4 mL)Was slowly added dropwise to a solution of 2-bromo-5H-pyrrolo [2,3-b] pyrazine-7-carboxylic acid (60%, 4.00 g, 8.26 mmol) in dichloromethane (150 mL)Reaction at room temperature for 2 h. Concentrated under reduced pressure,The residue was dissolved in dichloromethane (120 mL)Cyclobutylamine (2.2 mL, 26 mmol) and triethylamine were added(2.4 mL) was added and the reaction was carried out overnight. The reaction was quenched with water (150 mL)Dichloromethane (150 mL x 3), and the organic layer was dried over anhydrous Na2SO4, (Eluent: Cl2CH2 / MeOH (v / v) = 30/1) to give 1.20 g of a tan solid Rate: 49.0%.

According to the analysis of related databases, 1422772-78-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd; Liu, Bing; Huang, Jiuzhong; Zhang, Yingjun; Xue, Yaping; Xing, Wei; Xu, Juan; Wu, Zuping; Yu, Tianxi; (106 pag.)CN106432246; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

To a solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1.4 g,5.22 mmol) in ethanol (20 mL) was added sulfuric acid (0.5 mL) at 0 C. and the mixture was stirred at 80 C. for 1 hour. After cooling the reaction mixture was quenched with ice and extracted with ethyl acetate. The organic layer was washed with water,brine,dried over anhydrous sodium sulfate,filtered and concentrated in vacuo. The crude material was purified using flash chromatography (10% ethyl acetate/hexane) to provide ethyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate as a brown liquid (1.4 g,80% yield): MS (ES) m/z 272 (M+H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ACLARIS THERAPEUTICS, INC.; JACOBSEN, Eric Jon; ANDERSON, David Randolph; BLINN, James Robert; HOCKERMAN, Susan Landis; HEIER, Richard; MUKHERJEE, Paramita; (196 pag.)US2020/48262; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1422772-78-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1422772-78-8 name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 22-Bromo-5H-pyrrolo[2,3-b razine-7-carboxylic acid methyl esterTo a stirred solution of 2-bromo-5H-pyrrolo [2,3-b]pyrazine-7-carboxylic acid (0.527 g, 2.18 mmol) in 50 mL of methanol was added H2SO4 (1.5 mL) slowly at room temperature. The reaction mixture was stirred at reflux for 16 h. The solvent was evaporated at 40C under reduced pressure then the residue was suspended in 5 mL of water and treated with solidNaHC03 until pH = 7. The solution was extracted with ethyl acetate (90 mL), then the organics were washed with water (20 mL), brine (20 mL) and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the solvent was evaporated at 40C under reduced pressure to give a crude product, which was purified by column chromatography (silica gel, 200 – 300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (1 :1 , v/v) to give 2- bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid methyl ester (0.24 g, 43 %) as a white solid. LCMS: (M+H)+ = 278; 1H NMR (300 MHz, DMSO-d6): ? 8.62 (s, 1H), 8.48 (s, 1H), 3.91 (s,3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem